US 12,319,713 B2Granted

3,4-thiazolo-steroids and methods of making and using the same

AssigneeArkansas State University—Jonesboro

InventorMohammad Abrar Alam

Life of this patent

Estimating the term…

Abstract

3,4-thiazolo steroids are provided herein. Also provided herein are methods of making and using the same for the inhibition of cell proliferation or the killing of cells.

Claims12

Dependent claims

A compound of formula

or a salt thereof
wherein R1 is selected from
(1) —NR7AR7B and R7A and R7B are independently selected from hydrogen;
acetyl;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclylalkyl;
or
(2) hydrogen, a branched or unbranched, substituted or unsubstituted C1-C12 alkyl, a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl, a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl, a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl, a branched or unbranched, substituted or unsubstituted C6-C12 aryl, a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl, or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or
(3) —NR7AR7B and R7A and R7B together are selected from a branched or unbranched, substituted or unsubstituted C2-C12 alkylene;
a branched or unbranched, substituted or unsubstituted C2-C12 ether;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
and
wherein
(1) R4A and R4B are each hydrogen and
(A) one of R2 or R3 is selected from hydrogen and the other from a hydroxyl group;
or
(B) R2 and R3 together are selected from an oxo group;
or
(C) R2 and R3 together are selected from a ═N—NR10AR10B and
(i) R10A and R10B are independently selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or
(ii) R10A and R10B together is selected a branched or unbranched, substituted or unsubstituted C2-C12 alkylene;
a branched or unbranched, substituted or unsubstituted C2-C12 ether;
a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(D) R2 and R3 together are selected from =NOH;
or
(E) R2 and R3 together are selected from =NN(H)C(═Z)R8 wherein Z is selected from oxygen and sulfur and R8 is selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(F) one of R2 or R3 is selected from hydrogen and the other from —OC(═Z)R9 wherein Z is selected from oxygen and sulfur and R9 is selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(G) R1 is the —NR7AR7B and one of R2 or R3 is selected from hydrogen and the other from a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
or
(H) one of R2 or R3 is selected from a hydroxyl group and the other from C2-C12 alkynyl;
and
(2) R4A and R4B are together hydrogen and (A) R2 and R3 together are selected from a cyano group;
or
(B) R2 and R3 together are selected from a branched or unbranched,
substituted or unsubstituted C6-C12 aryl;
and
wherein
(1) R5A and R5B are together hydrogen and R6 is not present;
or
(2) each of R5A and R5B is hydrogen and R6 is hydrogen;
or
(3) one of R5A and R5 is hydrogen and the other is a hydroxyl group and R6 is selected from hydrogen or a hydroxyl group;
and
wherein n is equal to 0 or 1.

75 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/261,649Filed 22 Jul 2019 · us provisional application
Priority: 20 Jul 2018
Published: US 2021/0317160 A114 Oct 2021
Granted: 3 Jun 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 277/60
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings: condensed with carbocyclic rings or ring systems
C07J 71/0094
Sulfur-containing hetero ring: containing sulfur and nitrogen
A61P 35/00
Antineoplastic agents
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

Family

Application62/700,967Us provisional application · filed 20 Jul 2018
US 2021/0317160 A1Pre-grant publication · published 14 Oct 2021
US 12,319,713 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

3,4-thiazolo steroids are provided herein. Also provided herein are methods of making and using the same for the inhibition of cell proliferation or the killing of cells.

A compound of formula

or a salt thereof
wherein R1 is selected from
(1) —NR7AR7B and R7A and R7B are independently selected from hydrogen;
acetyl;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclylalkyl;
or
(2) hydrogen, a branched or unbranched, substituted or unsubstituted C1-C12 alkyl, a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl, a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl, a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl, a branched or unbranched, substituted or unsubstituted C6-C12 aryl, a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl, or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or
(3) —NR7AR7B and R7A and R7B together are selected from a branched or unbranched, substituted or unsubstituted C2-C12 alkylene;
a branched or unbranched, substituted or unsubstituted C2-C12 ether;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
and
wherein
(1) R4A and R4B are each hydrogen and
(A) one of R2 or R3 is selected from hydrogen and the other from a hydroxyl group;
or
(B) R2 and R3 together are selected from an oxo group;
or
(C) R2 and R3 together are selected from a ═N—NR10AR10B and
(i) R10A and R10B are independently selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
or a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or
(ii) R10A and R10B together is selected a branched or unbranched, substituted or unsubstituted C2-C12 alkylene;
a branched or unbranched, substituted or unsubstituted C2-C12 ether;
a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(D) R2 and R3 together are selected from =NOH;
or
(E) R2 and R3 together are selected from =NN(H)C(═Z)R8 wherein Z is selected from oxygen and sulfur and R8 is selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(F) one of R2 or R3 is selected from hydrogen and the other from —OC(═Z)R9 wherein Z is selected from oxygen and sulfur and R9 is selected from hydrogen;
a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkenyl;
a branched or unbranched, substituted or unsubstituted C2-C12 alkynyl;
a branched or unbranched, substituted or unsubstituted C3-C12 cycloalkyl;
a branched or unbranched, substituted or unsubstituted C6-C12 aryl;
a branched or unbranched, substituted or unsubstituted C6-C12 arylalkyl;
a branched or unbranched, substituted or unsubstituted C3-C12 heterocyclyl;
or a branched or unbranched, substituted or unsubstituted, secondary, tertiary, or quaternary amine;
or
(G) R1 is the —NR7AR7B and one of R2 or R3 is selected from hydrogen and the other from a branched or unbranched, substituted or unsubstituted C1-C12 alkyl;
or
(H) one of R2 or R3 is selected from a hydroxyl group and the other from C2-C12 alkynyl;
and
(2) R4A and R4B are together hydrogen and (A) R2 and R3 together are selected from a cyano group;
or
(B) R2 and R3 together are selected from a branched or unbranched,
substituted or unsubstituted C6-C12 aryl;
and
wherein
(1) R5A and R5B are together hydrogen and R6 is not present;
or
(2) each of R5A and R5B is hydrogen and R6 is hydrogen;
or
(3) one of R5A and R5 is hydrogen and the other is a hydroxyl group and R6 is selected from hydrogen or a hydroxyl group;
and
wherein n is equal to 0 or 1.

75 more elements

Facts

Application

17/261,649Filed 22 Jul 2019 · us provisional application

Priority

20 Jul 2018

Published

US 2021/0317160 A114 Oct 2021

Granted

3 Jun 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 277/60
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings: condensed with carbocyclic rings or ring systems
C07J 71/0094
Sulfur-containing hetero ring: containing sulfur and nitrogen
A61P 35/00
Antineoplastic agents
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links